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The Empty Chair Test™: When Your Mouth Can No Longer Carry the Funding Interview
Recently, I ended one of my free webinars, The Evidence Before the Ask™: What Your Business Must Prove Before You Seek Funding, with a photograph of an empty chair.
The question beside it was simple:
If you weren't in the room, would your evidence be convincing enough to earn the funder’s trust?
I chose that image deliberately.
Because too many founders still walk into funding conversations believing that passion, effort, revenue and a compelling explanation will somehow carry their "financial ask".
Then, the lender starts asking questions.
And suddenly the conversation changes.
Can you show me?
Where's the cash flow?
What supports these projections?
How did you arrive at this amount?
What exactly will the money do?
How does the business repay it?
And when the answer lives mainly in the founder’s mouth rather than in the business records, “Not Yet” becomes considerably more likely.
But here's the part some founders don't want to hear:
That the financial system needs reform.
Women, Black founders and Caribbean businesses continue to experience real barriers to capital.
And we still have considerable work to do in preparing stronger financial asks.
Both things can be true.
Your mouth can explain the business. It cannot become the evidence for the business.
🔴The fear didn't appear from nowhere
Women have a complicated relationship with money.
Especially women from communities where scarcity, caregiving and making-do have been normalized across generations.
Growing up, I watched mothers, grandmothers and aunties stretch money until it almost developed elastic properties.
They saved.
Negotiated.
Threw susus.
Managed households.
Found school money.
Emergency money.
Funeral money.
Business money.
Yet, many women still say:
“I’m just not good with money.”
Really?
Or have we failed to recognize those capabilities as "financial intelligence" because nobody put a formal name around them?
Here's another layer.
For generations, women lived inside systems in which financial authority was assumed to belong to men.
Some of that history still sits quietly underneath our behavior.
And contemporary evidence suggests the hesitation is real.
The Federal Reserve’s 2025 Small Business Credit Survey found that among Black-owned firms that didn't apply for financing, 44% were discouraged because they believed they would not be approved. Only 5% of white-owned nonapplicants gave the same reason. Another 24% of Black nonapplicants described themselves as "debt averse".
Read that again.
The lender hadn't rejected them.
Many had already rejected themselves.
And that's what I mean when I say:
Some founders are taking themselves out of the funding game before the first whistle blows.
📌And the fear isn't irrational.
Goldman Sachs found in 2024 that Black small-business owners were more likely to have applied for loans or credit, yet less likely to receive the full amount requested. Additionally, more than a third of Black owners who had borrowed reported terms they considered predatory.
In the Caribbean, CDB research also points to financing hesitancy, documentation challenges and cultural barriers. Its stakeholder analysis found that some women entrepreneurs—particularly respondents in The Bahamas—associated debt with caregiving responsibilities, cultural expectations and heightened fear of business failure.
So no, fear didn't appear from nowhere.
But we cannot allow fear to become the Chief Financial Officer of the business.
🔴When prudence starts becoming avoidance
Recently, I attended a networking event filled with very successful women.
What surprised me was how often the language of financial success came back to one thing:
“I pay cash.”
They saved for equipment.
Boasted about never needing a loan.
Talked about banks calling them with offers they refused.
And underneath some of that language, I heard fear.
But hear me when I say this: There's nothing inherently wrong with self-financing.
The problem comes when saving becomes the only acceptable capital strategy.
Because the same cash may also have to absorb:
a slow season,
equipment failure,
a lawsuit,
a fire,
delayed receivables,
payroll,
an unexpected contract,
or the opportunity you didn't know was coming.
Therefore, a business that continually consumes its liquidity to fund long-term assets may look debt-free while becoming increasingly fragile.
That's why I keep asking:
"When did the relationship between founder and lender become automatically adversarial?"
Capital is a tool.
Savings are a tool.
Debt is a tool.
Investment is a tool.
The question isn't whether any one of them is morally superior.
The question is whether the founder understands when each one makes commercial sense.
🔴I don’t need a loan” misses the point
Another sentence I hear regularly is:
“I don’t need a loan, so fundability isn’t for me.”
But fundability isn't another word for borrowing.
Fundability is about whether an external decision-maker can look at your business and say:
I understand what I'm looking at.
Because a lender needs clarity.
So does an investor.
A grant maker.
A corporate buyer.
A strategic partner.
A sponsor.
A potential acquirer.
That's why I keep insisting that financial literacy and fundability are not interchangeable.
Financial literacy tells me something about what you understand.
Fundability asks: What can the business prove?
Many founders already possess considerable pieces of that evidence.
Revenue exists.
Customers exist.
Demand exists.
Records exist somewhere.
The problem is that the evidence is scattered across bank accounts, WhatsApp messages, invoices, spreadsheets, the founder’s memory and three different notebooks.
Sometimes the evidence isn't missing. It's simply too disorganized to make the case.
🔴Put the founder outside the room
This is where the Empty Chair Test™ begins.
Imagine you're sitting across from a funder.
Then get up.
Leave.
Your chair is empty.
Your files now have to continue the conversation.
Can they?
For me, three areas are non-negotiable.
🪙Cash flow
Not: “I’m making money.”
Show how money enters and leaves the business.
Show the timing.
The obligations.
The pressure points.
The receivables.
The debt.
The capacity to absorb repayment.
Revenue may tell us money entered.
Cash flow tells us whether the business can breathe.
🪙Projections
Not numbers created the night before the application because somebody told you the lender needed a forecast.
What is the business likely to do?
Why?
What evidence supports that expectation?
What assumptions are you making?
What happens if those assumptions change?
🪙Credible use of funds
Not: “I need $200,000 to grow.”
What exactly will that money fund?
Why that amount?
What business outcome should it produce?
And how does that outcome support repayment, resilience or growth?
Money has a job. Your Use of Funds Plan should tell us exactly what that job is.
🔴Your projections should know your customers
One of the best business lessons I ever learned came from a man selling doubles at Piarco International Airport.
Mr. Kamal Colai-better known around the airport as Red Box-built a reputation through something deceptively simple: he listened.
He greeted customers.
He remembered preferences.
He extended credit selectively.
He added products customers wanted.
He accommodated different currencies.
He developed call-in business.
Demand eventually extended beyond the airport and beyond Trinidad.
But the lesson here, isn't about doubles
It's about "customer intelligence".
Red Box moved from selling to solving.
And that's why I become frustrated when founders treat craft markets and pop-ups merely as places to make sales.
A market is a live research environment.
Who stopped?
Who bought?
What did they ask for?
What did they refuse?
What sold fastest?
What did they want next?
Where did price resistance appear?
What patterns repeated?
That information belongs inside your Evidence File.
It should influence your projections.
It may even determine your Use of Funds.
Because projections should not be dreams manufactured for a funder. They should emerge from what your business is learning.
Truth is, any business can move from selling to solving—but only if the founder listens closely enough to see what the customer is actually asking for.
🔴What fear looks like in the accounts
So what happens when the evidence exists, but founders still avoid the ask?
Fear starts behaving like an accounting line.
It shows up as delayed investment.
Cash hoarding.
Underpricing.
Missed applications.
Tiny projections.
Refusal to seek professional help.
Funding requests barely large enough to complete the project—with no room for delay, error or working-capital pressure.
And sometimes it shows up as saying no to growth before anyone else has the opportunity to say yes.
That may be the most expensive form of fear.
Because it rarely appears on the profit-and-loss statement.
Yet, the business pays for it.
In slower growth.
Lost capacity.
Missed contracts.
Weak margins.
Deferred decisions.
Opportunity never pursued.
So here's the question I want you to carry into the final quarter of 2026:
What would you do if you weren’t afraid? And how much of that fear has already become an accounting line?
🔴Make Q4 a "proof-building" quarter
I'm not going to tell you to “finish the year strong.”
That phrase has been beaten to death.
Instead, use the final quarter of 2026 to make your business easier to understand.
Easier to verify.
Easier to trust.
Easier to fund.
Get your cash flow visible.
Organize the evidence your customers are already giving you.
Build projections from something stronger than optimism.
Decide what capital would actually do.
Ask for help where you need it.
And then come back to the Empty Chair.
If you walked out of the room tomorrow, would your business become less credible?
If the answer is yes, there's work to do.
The system may still need reform.
The lender may still say no.
But this time, make sure the rejection isn't happening because your mouth was asked to carry a case your business should have been able to prove.
Because the goal isn't to make yourself irrelevant.
The goal is to stop being the only evidence that the business works.
That's the work we're doing inside Power Circle™ and The Fundable Lab™: creating spaces where women can talk honestly about money, examine the evidence, see what's missing and strengthen it.
Because when the chair is empty, the business still needs to speak.
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